Sodium hydride → N-(3,4-dimethyl-5-isoxazolyl)-2-(3,4-methylenedioxybenzyl)benzo[b]thiophene-3-sulfonamide

HRID 1166908Notes

Reaction equation

HRID 1166908 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH2:8])[O:4][N:3]=1.[H-].[Na+].[CH2:11]1[O:33][C:32]2[CH:31]=[CH:30][C:15]([CH2:16][C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[S:26](Cl)(=[O:28])=[O:27])=[CH:14][C:13]=2[O:12]1>C1COCC1>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:26]([C:18]2[C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[S:21][C:17]=2[CH2:16][C:15]2[CH:30]=[CH:31][C:32]3[O:33][CH2:11][O:12][C:13]=3[CH:14]=2)(=[O:28])=[O:27])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 883175-Amino-3,4-dimethylisoxazoleHCID 229983852-[3,4-(Methylenedioxy)benzyl]-benzo[b]thiophene-3-sulfonylchloride

Product 1

HCID 22998423N-(3,4-dimethyl-5-isoxazolyl)-2-(3,4-methylenedioxybenzyl)benzo[b]thiophene-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3,4-dimethyl-5-isoxazolyl)-2-(3,4-methylenedioxybenzyl)benzo[b]thiophene-3-sulfonamide was prepared in the same manner as described in Example 41. Reaction of 3,4-dimethyl-5-aminoisoxazole (1.0 mmoles, 0.11 g), NaH (2.5 mmoles, 60 mg) and 2-[3,4-(methylenedioxy)benzyl]-benzo[b]thiophene-3-sulfonylchloride (1.1 mmoles, 0.40 g) in THF (6 ml) yielded, after flash chromatography using 50% ethyl acetate/hexanes followed by recrystallization from chloroform and hexanes, 0.35 g (79%) of a tan solid, m.p. 135-137° C.

Workup

  1. customyielded
  2. customfollowed by recrystallization from chloroform and hexanes, 0.35 g (79%) of a tan solid, m.p. 135-137° C.

Sources & evidence

ORD record
ord-52bf1d7d98ba4a92a23e58ab0a402f25
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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